Windows Turns 30: A History, Told Through Microsoft's Terrible Ads

Microsoft turned 30 on Friday, and what a joyous occasion it was. Windows is once again a force to be reckoned with, and all it took was Windows 10 not being a complete dumpster fire of a UI. As the operating system has changed, so has Microsoft’s approach to sales—from one strain of crazy to another.

I started poking around in Windows history and stumbled across these beloved gems of computing yesteryear. Let’s take a brief step back through history, and try to understand what’s assaulting our eyeballs.

This is probably the best known Microsoft advert ever. Former CEO Steve Ballmer was famously eccentric when it came to selling all things Microsoft, and it wasn’t any different in 1985. I won’t pretend that I remember the 80s, but I find it hard to believe that a multi-million dollar company shot this advert and thought “Yeah, sure. Run it.” Did Ballmer even watch it? What about Miami Vice? What’s going on with Nebraska? So many questions.

Either way, it’s glorious tech history. He even reprised his overexcited huckster role for Windows XP years later.

Now, this is a Japanese commercial. Even though I lived a good six months in the country, I’m still going to chalk this up to being a cultural mistranslation. A fancy old dude has a spoiled son who really wants Windows 3.1. It’s then served to him on a silver platter (to eat?) and then a mouse encircles him and he like...teleports...or something? Into the internet maybe? Or...whatever. I have no idea.

If you wanted to say “How do you do, fellow kids” in 1995, you slappedFriends’ stars Jennifer Aniston and Matthew Perry in your video user guide. This is so 90s it’s actually painful to watch. If they would’ve added an outro track from Ace of Base my head probably would’ve exploded from nostalgia.

At some point, you have to respect Ballmer and Gates’ ability to simply not give a fuck.